Chapter 10 – Studies in the Synthesis of Biaryl Natural Products: The 6,6′-Binaphthopyranones

Efficient and enantioselective syntheses of a family of 6,6′-binaphthopyranone natural products (viriditoxin, pigmentosin A, talaroderxine A, and talaroderxine B) are reported. A vanadium-catalyzed oxidative coupling provides the key axial chirality in high diastereoselectivity. A unified Michael–Dieckman annulation strategy allows for access to the coupling precursors from an orthogonally protected orsellinate ester and the requisite α,β-unsaturated pyranones, which are synthesized through various enantioselective strategies. Herein, we report the successful syntheses of these natural products and their use in our continued efforts in studying the bacterial cell division protein, FtsZ.